Six Timeless Lessons for Success From a NYC Icon and Self-Made Mogul

An exclusive interview with real estate magnate Steve Witkoff: lessons from life, luck, and a long friendship with the POTUS.

Gleaning secrets to success has become a cottage industry. Everyone and their mother has their own “nine keys for success.” I do too, I admit–as evidenced when I write articles trying to give new perspective about the path to prosperity.

So it was surprisingly refreshing when I talked with New York City real estate mogul Steve Witkoff. He’s the chairman, CEO, and founder of Witkoff, a well-known development and investment firm.

1. Success belongs to those who believe in it the most

Read this again to yourself. Slowly. Out loud. It’s the most common thing I hear across all the redonkulously successful people I interview.

As Witkoff told me, “Successful people have belief, sure. But it’s so easy to be knocked off of that belief. Don’t waver.”

Witkoff started with a $40,000 deal–he only had $20,000 to his name and had to borrow the rest from his father (who had not much more than that himself). It takes a lot of self-belief to come a long way, baby.

2. Know your business from the ground up or you’ll get ground-up

Success isn’t for pretenders. It comes from truly knowing your business, all the intricacies and unsexy details. Witkoff learned that way and hires people willing to do the same.

He emphasized this belief with a story from his long-time friend and fellow real estate developer Donald Trump (who has another side-hustle you might be aware of).

Donald Trump, Wharton grad, sat in his father’s office, watching his dad pay an exterminator bill. Trump’s father asked the exterminator to leave behind his spraying machine. He then turned to Donald and asked him to take it to a chemical analysis lab because maybe they could replicate the spray and do the job themselves.

To Witkoff, that’s getting involved in a business from the ground up, something he treasures.

3. Know how you want to be successful

It’s not enough to just be successful, it’s how you go about it. Witkoff has done so with a sense of purpose–to have an impact on others, to show gratitude, to never let his ego get ahead of a sense of where he came from, and to always appreciate how fortunate he is (something he does constantly, even after the tragic loss of his eldest son).

4. You can start with humility, or get it handed to you

Witkoff told me of his early days in real estate in the late 1980’s where all he and his partner wanted to do was be “the deal guy”. He dressed the part and hired others to manage his properties because “we were above that.”

They attributed early success to being smarter than everyone else, not due to a good market.

Then, in 1990, they got a call from an oil company–the bills weren’t being paid and the property manager had been embezzling millions from them.

Witkoff learned humility and that he and his partner weren’t the deal guys they thought they were. From that point forward, he learned how to get involved in all the nitty-gritty and hard labor parts of property management.

You can’t do it all alone. Luck factors in, and it takes a great team that deserves credit when it’s due.

5. Hard work and hard knocks are your guides

The School of Hard Knocks is a real thing–one that Witkoff says has molded him immeasurably. In other words: Learn from your mistakes, so you don’t repeat them.

When I asked what advice he had for millennial success hunters, he said:

“Understand that success doesn’t happen immediately. It takes a willingness to work really, really hard. Stick with what you’re doing and stop skipping around so much. If you’re disrespected, yes, leave, but don’t worry about your peers and what they’re making–develop that skill set–no one can take that away from you.”

6. Learn to work well with people from all walks of life, not just your walk of life

This is the biggest secret to Witkoff’s success. Whether it’s dealing with high-powered bankers or economically challenged building tenants just trying to get by, it’s critical to see things from the others’ point of view and to work with them with insight and empathy.

There’s a saying about New York City: “If you can make it there, you can make it anywhere.” I suspect Steve Witkoff would indeed have made it anywhere, but not in any way.

His way.

The good ol’ fashioned way.

This article by Scott Mautz also appeared on Inc.com. To read more Inc. articles by Scott Mautz, click here.